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675725

Sigma-Aldrich

4-Bromo-1-butyne

97%

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Synonym(s):
1-Bromo-3-butyne
Empirical Formula (Hill Notation):
C4H5Br
CAS Number:
Molecular Weight:
132.99
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

refractive index

n20/D 1.481

density

1.417 g/mL at 25 °C

SMILES string

BrCCC#C

InChI

1S/C4H5Br/c1-2-3-4-5/h1H,3-4H2

InChI key

XLYOGWXIKVUXCL-UHFFFAOYSA-N

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1 of 4

This Item
337528274372249904
4-Bromo-1-butyne 97%

675725

4-Bromo-1-butyne

Allyl bromide reagent grade, 97%, contains ≤1000 ppm propylene oxide as stabilizer

337528

Allyl bromide

3,3-Dimethylallyl bromide 95%, contains silver wool as stabilizer

274372

3,3-Dimethylallyl bromide

3,3-Dimethylallyl bromide technical grade, ~90%

249904

3,3-Dimethylallyl bromide

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

refractive index

n20/D 1.481

refractive index

n20/D 1.469 (lit.)

refractive index

n20/D 1.489 (lit.)

refractive index

n20/D 1.489 (lit.)

density

1.417 g/mL at 25 °C

density

1.398 g/mL at 25 °C (lit.)

density

1.29 g/mL at 20 °C (lit.)

density

1.29 g/mL at 20 °C (lit.)

General description

4-Bromo-1-butyne is commonly used as a reactant. It serves as a source of alkyl halides for the introduction of bromo functionality into the molecule.

Application

4-Bromo-1-butyne is used as a reactant in the synthesis of:
  • Macrocycles by cobalt-mediated [2+2+2] co-cyclotrimerization.
  • 2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3+2] cycloaddition.
  • Intramolecular 1,3-dipolar cycloaddition to synthesize 1,3,4-oxadiazoles.
  • Lactones bearing alkynes for reductive cyclization in the preparation of azulene derivatives.
  • Substituted α-pyrones by gold-catalyzed coupling reactions.

pictograms

FlameSkull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Flam. Liq. 3 - Skin Sens. 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

75.0 °F

flash_point_c

23.9 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Synthesis of macrocycles via cobalt-mediated [2+ 2+ 2] cycloadditions.
Bonaga LVR, et al.
Journal of the American Chemical Society, 127(10), 3473-3485 (2005)
A facile synthesis of N-C linked 1, 2, 3-triazole-oligomers
V Fiandanese, et al.
Tetrahedron, 67, 5254-5260 (2011)
Intramolecular Diels- Alder/1, 3-dipolar cycloaddition cascade of 1, 3, 4-oxadiazoles.
Elliott GI, et al.
Journal of the American Chemical Society, 128(32), 10589-10595 (2006)
Reductive Cyclization Cascades of Lactones Using SmI2- H2O.
Parmar D, et al.
Journal of the American Chemical Society, 133(8), 2418-2420 (2011)
Intermolecular and Selective Synthesis of 2, 4, 5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+ 2] Cycloaddition.
Davies PW, et al.
Angewandte Chemie (International Edition in English), 50(38), 8931-8935 (2011)

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